my background is jazz and blues. all my life i have hated my falsetto and tried to stay in chest voice. i had no control and thus no confidence, and the sound was so different from what i usually do that the transitions sounded really klunky and unprofessional. i sounded like two totally different people, badly edited together. it really limits me, and as part of looking around for more singing connections i am trying to address it.

i finally started practising covering a song i clicked with--it mercilessly travels back and forth across my register break. i've been at it for about a week. its the first time i have been able to relax my throat and be at all expressive in falsetto. from years of cringing away, i still cant always stop myself from staying in chest voice, you can hear me squeezing it out half the time. for example i should be singing the word "vain" in falsetto, and i'm dropping to chest voice too soon, and it screws up the pitch and you can totally hear it. i feel like i am progressing because i can get moments that sound OK. but i am so inconsistent still. for another thing you can hear how much blues there is in my voice. i am just now seeing that i need to develop more control over it, or it takes over. it has to be a choice, not some kind of default setting

The biggest issue I find with students and the break and mix from chest to head voice is weight. The higher you go in your chest voice, the more heaviness will exist. To mix and shift, you need to think of the sound as having less weight the closer it gets to your break.
Conversely, you can start up in your headvoice and slowly descend and add weight as you go. As a general rule though, singers tend to put too much weight in their sound, so most of us must concentrate on not letting the heaviness creep in.
The challenge lies in isolating this idea of "weight" in your sound and then making it the only variable. Breath, resonance, vowel placement, energy, these should all remain constant through your range.

I would say that the break between your head voice and chest voice is 90% mental. All you have to do is work your head voice to make it stronger. (Side note... what you're doing here would be called head voice and not falsetto. Most of the time, that break is called falsetto for men. For women, it is called head voice. There is such a thing as female falsetto, but it's a different thing, and it's not what you're doing.) Anyway, you have to work your head voice to the point of having a little bit of power to it, then your transition between head voice and chest voice won't really be a transition at all. Work on getting your placement into a consistent place so that you're not delineating 2 "voices." This will take some work with your chest voice too. Have fun! You're doing great!
Source: music ed degree, high school choir teacher

can you clarify what you mean by "placement"? i havent had formal coaching. i go to workshop, but its jazz, its about fitting in with a trio and scatting and signalling and responding to changes on the fly. nobody ever says anything like "hey, watch your 'placement'"

All that stuff is good, too. Placement means where you are letting your voice resonate physically. You can sing from your throat (tedious, tiresome, won't do you much good in the long run), towards the back of your mouth, middle of your mouth, or front of your mouth. You want to try to resonate forward and high, so that you feel like you a resonating throughout your head. Don't "swallow" your sound. It's one of those things that I could demonstrate in 2 seconds but it rather complicated to describe here. Hope that makes sense.